data_global #======================================================== _publ_contact_author ; Agnieszka Rybarczyk-Pirek Department of Crystallography and Crystallochemistry University of \/L\'od\'z Pomorska 149/153 PL-90236 \/L\'od\'z Poland ; _publ_contact_author_phone '010 48 1033 42 6355740' _publ_contact_author_fax '010 48 1033 42 6790447' _publ_contact_author_email 'arybarcz@krysia.uni.lodz.pl' _publ_contact_letter ; This CIF file contains details of the two crystal structures which are part of manuscript submitted to New J. Chem. for publication on March 11, 2002. ; _publ_requested_journal 'The Journal of Physical Chemistry' _publ_section_title ; ; loop_ _publ_author_name _publ_author_address ' RYBARCZYK-Pirek, Agnieszka J.' ; Department of Crystallography and Crystallochemistry University of \/L\'od\'z Pomorska 149/153 PL-90236 \/L\'od\'z Poland ; ' GRABOWSKI, S\/awomir J.' ; Department of Crystallography and Crystallochemistry University of \/L\'od\'z Pomorska 149/153 PL-90236 \/L\'od\'z Poland ; ' NAWROT-MODRANKA, Jolanta' ; Laboratory of Bioinorganic Chemistry Faculcy of Chemistry Medical University Muszy\'nskiego 1 PL-90236 \/L\'od\'z Poland ; ' MA\/LECKA, Magdalena' ; Department of Crystallography and Crystallochemistry University of \/L\'od\'z Pomorska 149/153 PL-90236 \/L\'od\'z Poland ; _publ_section_references ; De Meulenar, J., Tompa, H. (1965). Acta Cryst. 19, 1014-1018. Farrugia, L.J., J. Appl. Cryst. (1999) 32, 837-838 Kuma Diffraction (1992). Kuma KM4 Diffractometer Software. Wroc\/law, Poland. Molecular Structure Corporation (1989a). MSC/AFC Diffractometer Control Software. MSC, 3200 Research Forest Drive, The Woodlands, TX. 77381, USA. Molecular Structure Corporation (1989b). TEXSAN. TEXRAY Structure Analysis Software. MSC, 3200 Research Forest Drive, The Woodlands, TX. 77381, USA. Nardelli, M. (1996). J. Appl. Cryst. 29, 296-300. Sheldrick, G.M. (1986) SHELXS86. Program for Crystal Structure Solution. University of G\"ottingen, Germany. Sheldrick, G.M. (1997). SHELXL97. Program for Crystal Structure Analysis. University of G\"ottingen, Germany. Spek, A.L. (1998). PLATON. Molecular Geometry Program vers. of November 1998. University of Utrecht, The Netherlands ; #=================================================END data_comp1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H19 N2 O6 P' _chemical_formula_sum 'C23 H19 N2 O6 P' _chemical_formula_weight 450.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.304(1) _cell_length_b 10.396(1) _cell_length_c 24.695(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.46(1) _cell_angle_gamma 90.00 _cell_volume 2102.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 95 _cell_measurement_theta_min 10.71 _cell_measurement_theta_max 35.25 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 1.41 _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method ; measured by flotation in a mixture of KI and KBr in water solution ; _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.546 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.4187 _exptl_absorpt_correction_T_max 0.8883 _exptl_absorpt_correction_T_ave 0.4690 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM-4 diffractometer' _diffrn_measurement_method '/w scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% '<2%' _diffrn_reflns_number 4332 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 80.08 _reflns_number_total 4235 _reflns_number_gt 3020 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM-4 software (1992)' _computing_cell_refinement 'Kuma KM-4 software (1992)' _computing_data_reduction 'Dataproc in Kuma KM-4 software (1996)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc' _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.9502P] where P=(Fo^2^+2Fc^2^)/3' ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0065(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4235 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_restrained_S_all 1.206 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.25982(7) 0.20028(5) 0.18771(2) 0.04229(17) Uani 1 d . . . O2 O 0.2670(2) 0.13572(16) 0.24010(7) 0.0542(4) Uani 1 d . . . N3 N 0.1284(2) 0.31991(18) 0.17934(8) 0.0458(5) Uani 1 d . . . C31 C 0.0070(3) 0.3421(3) 0.21451(11) 0.0533(6) Uani 1 d . . . H311 H 0.019(3) 0.273(3) 0.2412(12) 0.067(8) Uiso 1 d . . . H313 H -0.103(4) 0.334(3) 0.1915(12) 0.077(9) Uiso 1 d . . . H312 H 0.021(4) 0.429(3) 0.2321(13) 0.081(10) Uiso 1 d . . . N4 N 0.1350(2) 0.39766(18) 0.13434(8) 0.0433(4) Uani 1 d . . . O21 O 0.42643(18) 0.25793(14) 0.17500(6) 0.0443(4) Uani 1 d . . . C22 C 0.5176(2) 0.3501(2) 0.20912(9) 0.0399(5) Uani 1 d . . . C23 C 0.5576(3) 0.4620(2) 0.18443(11) 0.0488(5) Uani 1 d . . . H231 H 0.514(3) 0.473(3) 0.1462(11) 0.063(8) Uiso 1 d . . . C24 C 0.6559(3) 0.5512(3) 0.21545(13) 0.0575(7) Uani 1 d . . . H241 H 0.683(4) 0.629(3) 0.1974(12) 0.076(9) Uiso 1 d . . . C25 C 0.7130(3) 0.5280(3) 0.27030(12) 0.0587(7) Uani 1 d . . . H251 H 0.789(3) 0.592(3) 0.2926(12) 0.071(9) Uiso 1 d . . . C26 C 0.6705(3) 0.4163(3) 0.29434(12) 0.0555(6) Uani 1 d . . . H261 H 0.700(3) 0.398(3) 0.3306(12) 0.068(9) Uiso 1 d . . . C27 C 0.5718(3) 0.3255(2) 0.26389(10) 0.0467(5) Uani 1 d . . . H271 H 0.539(3) 0.246(3) 0.2795(11) 0.061(8) Uiso 1 d . . . O11 O 0.2094(2) 0.11684(15) 0.13445(7) 0.0515(4) Uani 1 d . . . C12 C 0.2948(3) 0.0045(2) 0.12407(9) 0.0433(5) Uani 1 d . . . C13 C 0.3928(4) 0.0092(3) 0.08453(12) 0.0625(7) Uani 1 d . . . H131 H 0.396(3) 0.087(3) 0.0657(12) 0.068(9) Uiso 1 d . . . C14 C 0.4751(4) -0.1021(4) 0.07391(14) 0.0724(9) Uani 1 d . . . C15 C 0.4562(4) -0.2138(3) 0.10185(13) 0.0639(7) Uani 1 d . . . H151 H 0.517(4) -0.294(3) 0.0929(12) 0.083(10) Uiso 1 d . . . C16 C 0.3557(4) -0.2171(3) 0.14023(12) 0.0593(7) Uani 1 d . . . H161 H 0.343(4) -0.301(3) 0.1587(12) 0.081(9) Uiso 1 d . . . C17 C 0.2733(3) -0.1070(2) 0.15161(11) 0.0505(6) Uani 1 d . . . H171 H 0.201(4) -0.105(3) 0.1774(12) 0.079(10) Uiso 1 d . . . C5 C 0.0389(3) 0.4948(2) 0.12510(9) 0.0423(5) Uani 1 d . . . O61 O -0.0336(2) 0.77663(16) 0.03150(7) 0.0551(4) Uani 1 d . . . H51 H -0.042(3) 0.516(2) 0.1494(10) 0.048(7) Uiso 1 d . . . C62 C -0.0520(3) 0.6904(2) 0.07222(10) 0.0495(6) Uani 1 d . . . O621 O -0.1552(3) 0.7149(2) 0.09974(9) 0.0759(6) Uani 1 d . . . C63 C 0.0535(3) 0.5786(2) 0.07905(9) 0.0405(5) Uani 1 d . . . H631 H 0.538(4) -0.096(3) 0.0461(15) 0.100(12) Uiso 1 d . . . C64 C 0.1640(3) 0.5591(2) 0.04462(9) 0.0416(5) Uani 1 d . . . O641 O 0.2644(2) 0.45798(17) 0.04944(8) 0.0557(5) Uani 1 d . . . H641 H 0.246(4) 0.411(3) 0.0783(13) 0.083(11) Uiso 1 d . . . C65 C 0.2927(3) 0.6379(3) -0.03410(11) 0.0568(6) Uani 1 d . . . H651 H 0.360(3) 0.564(3) -0.0303(11) 0.061(8) Uiso 1 d . . . C66 C 0.3036(4) 0.7324(3) -0.07221(12) 0.0719(9) Uani 1 d . . . H661 H 0.383(4) 0.721(3) -0.0953(14) 0.088(11) Uiso 1 d . . . C67 C 0.2038(5) 0.8392(3) -0.07534(12) 0.0729(9) Uani 1 d . . . H671 H 0.206(4) 0.900(4) -0.1030(15) 0.100(12) Uiso 1 d . . . C68 C 0.0914(4) 0.8538(3) -0.04071(11) 0.0609(7) Uani 1 d . . . C69 C 0.0807(3) 0.7583(2) -0.00244(10) 0.0482(5) Uani 1 d . . . C70 C 0.1797(3) 0.6502(2) 0.00186(9) 0.0441(5) Uani 1 d . . . H681 H 0.023(4) 0.925(3) -0.0401(12) 0.077(10) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0461(3) 0.0351(3) 0.0456(3) 0.0027(2) 0.0074(2) 0.0019(2) O2 0.0634(11) 0.0461(9) 0.0531(10) 0.0113(8) 0.0098(8) 0.0007(8) N3 0.0507(11) 0.0417(10) 0.0487(11) 0.0091(9) 0.0189(8) 0.0069(8) C31 0.0538(15) 0.0578(15) 0.0528(15) 0.0076(14) 0.0218(12) 0.0044(12) N4 0.0479(10) 0.0387(9) 0.0448(10) 0.0046(8) 0.0123(8) 0.0046(8) O21 0.0451(8) 0.0423(8) 0.0467(9) -0.0061(7) 0.0113(6) 0.0007(7) C22 0.0381(10) 0.0365(10) 0.0463(12) -0.0046(10) 0.0109(9) 0.0065(9) C23 0.0499(13) 0.0426(12) 0.0537(15) 0.0040(11) 0.0083(11) 0.0056(10) C24 0.0588(15) 0.0410(13) 0.0735(19) 0.0004(13) 0.0132(13) -0.0013(11) C25 0.0561(15) 0.0500(14) 0.0699(18) -0.0157(13) 0.0099(13) -0.0037(12) C26 0.0574(15) 0.0585(15) 0.0498(15) -0.0066(13) 0.0065(11) 0.0025(12) C27 0.0495(13) 0.0426(12) 0.0493(13) 0.0001(11) 0.0118(10) 0.0033(10) O11 0.0544(10) 0.0407(8) 0.0553(10) -0.0056(7) -0.0029(7) 0.0050(7) C12 0.0429(12) 0.0383(11) 0.0464(13) -0.0059(10) 0.0005(9) -0.0020(9) C13 0.0725(18) 0.0571(16) 0.0598(17) -0.0006(14) 0.0169(14) -0.0107(14) C14 0.0683(18) 0.086(2) 0.0684(19) -0.0220(18) 0.0264(15) -0.0082(16) C15 0.0595(16) 0.0596(16) 0.0701(19) -0.0201(15) 0.0034(13) 0.0063(13) C16 0.0666(17) 0.0419(13) 0.0655(17) -0.0048(13) -0.0006(13) 0.0003(12) C17 0.0527(14) 0.0433(12) 0.0562(15) -0.0027(11) 0.0115(11) -0.0035(10) C5 0.0447(12) 0.0392(11) 0.0447(12) -0.0009(10) 0.0125(9) 0.0030(9) O61 0.0620(10) 0.0465(9) 0.0571(11) 0.0095(8) 0.0108(8) 0.0144(8) C62 0.0539(13) 0.0447(12) 0.0512(14) 0.0026(11) 0.0124(10) 0.0110(10) O621 0.0805(14) 0.0725(13) 0.0838(14) 0.0163(11) 0.0404(11) 0.0353(11) C63 0.0428(11) 0.0367(11) 0.0424(12) -0.0009(9) 0.0083(9) 0.0031(9) C64 0.0426(11) 0.0380(11) 0.0441(12) -0.0033(9) 0.0066(9) 0.0018(9) O641 0.0600(11) 0.0502(10) 0.0617(11) 0.0068(9) 0.0246(9) 0.0173(8) C65 0.0634(16) 0.0607(16) 0.0495(14) -0.0033(13) 0.0183(12) -0.0045(13) C66 0.086(2) 0.080(2) 0.0545(17) -0.0006(16) 0.0245(15) -0.0203(18) C67 0.099(2) 0.0699(19) 0.0492(16) 0.0132(15) 0.0097(15) -0.0192(18) C68 0.0759(19) 0.0538(15) 0.0492(15) 0.0088(13) -0.0007(13) -0.0032(14) C69 0.0538(13) 0.0476(12) 0.0411(12) 0.0003(10) 0.0013(10) -0.0028(10) C70 0.0487(12) 0.0450(12) 0.0382(11) -0.0023(10) 0.0056(9) -0.0054(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O2 1.4501(17) . ? P1 O11 1.5738(16) . ? P1 O21 1.5857(16) . ? P1 N3 1.6450(19) . ? N3 N4 1.382(2) . ? N3 C31 1.453(3) . ? C31 H311 0.97(3) . ? C31 H313 1.00(3) . ? C31 H312 1.00(3) . ? N4 C5 1.284(3) . ? O21 C22 1.411(3) . ? C22 C27 1.378(3) . ? C22 C23 1.379(3) . ? C23 C24 1.381(4) . ? C23 H231 0.96(3) . ? C24 C25 1.381(4) . ? C24 H241 0.97(3) . ? C25 C26 1.376(4) . ? C25 H251 1.02(3) . ? C26 C27 1.388(3) . ? C26 H261 0.91(3) . ? C27 H271 0.97(3) . ? O11 C12 1.412(3) . ? C12 C17 1.370(3) . ? C12 C13 1.371(4) . ? C13 C14 1.390(4) . ? C13 H131 0.94(3) . ? C14 C15 1.372(5) . ? C14 H631 0.93(3) . ? C15 C16 1.363(4) . ? C15 H151 1.02(3) . ? C16 C17 1.386(4) . ? C16 H161 1.00(3) . ? C17 H171 0.95(3) . ? C5 C63 1.454(3) . ? C5 H51 0.99(2) . ? O61 C62 1.374(3) . ? O61 C69 1.379(3) . ? C62 O621 1.206(3) . ? C62 C63 1.448(3) . ? C63 C64 1.365(3) . ? C64 O641 1.335(3) . ? C64 C70 1.440(3) . ? O641 H641 0.90(3) . ? C65 C66 1.374(4) . ? C65 C70 1.400(3) . ? C65 H651 0.95(3) . ? C66 C67 1.379(5) . ? C66 H661 0.95(3) . ? C67 C68 1.374(4) . ? C67 H671 0.93(4) . ? C68 C69 1.383(4) . ? C68 H681 0.94(3) . ? C69 C70 1.387(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 P1 O11 117.18(10) . . ? O2 P1 O21 116.24(10) . . ? O11 P1 O21 99.44(9) . . ? O2 P1 N3 113.03(10) . . ? O11 P1 N3 103.41(10) . . ? O21 P1 N3 105.77(9) . . ? N4 N3 C31 120.70(19) . . ? N4 N3 P1 115.47(14) . . ? C31 N3 P1 123.78(17) . . ? N3 C31 H311 106.4(17) . . ? N3 C31 H313 107.8(17) . . ? H311 C31 H313 108(2) . . ? N3 C31 H312 111.1(18) . . ? H311 C31 H312 112(2) . . ? H313 C31 H312 111(2) . . ? C5 N4 N3 119.83(19) . . ? C22 O21 P1 122.58(13) . . ? C27 C22 C23 121.8(2) . . ? C27 C22 O21 121.1(2) . . ? C23 C22 O21 117.0(2) . . ? C22 C23 C24 119.0(2) . . ? C22 C23 H231 117.0(17) . . ? C24 C23 H231 124.0(17) . . ? C23 C24 C25 120.2(3) . . ? C23 C24 H241 117.9(18) . . ? C25 C24 H241 121.9(18) . . ? C26 C25 C24 120.0(3) . . ? C26 C25 H251 120.1(16) . . ? C24 C25 H251 119.9(16) . . ? C25 C26 C27 120.7(3) . . ? C25 C26 H261 123.5(19) . . ? C27 C26 H261 115.7(19) . . ? C22 C27 C26 118.3(2) . . ? C22 C27 H271 118.7(16) . . ? C26 C27 H271 123.0(16) . . ? C12 O11 P1 122.35(14) . . ? C17 C12 C13 121.7(2) . . ? C17 C12 O11 120.0(2) . . ? C13 C12 O11 118.3(2) . . ? C12 C13 C14 118.2(3) . . ? C12 C13 H131 116.7(18) . . ? C14 C13 H131 125.1(18) . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H631 124(2) . . ? C13 C14 H631 116(2) . . ? C16 C15 C14 120.3(3) . . ? C16 C15 H151 120.7(18) . . ? C14 C15 H151 118.9(18) . . ? C15 C16 C17 119.9(3) . . ? C15 C16 H161 117.5(18) . . ? C17 C16 H161 122.6(18) . . ? C12 C17 C16 119.3(2) . . ? C12 C17 H171 117.6(19) . . ? C16 C17 H171 123.1(19) . . ? N4 C5 C63 118.8(2) . . ? N4 C5 H51 121.6(14) . . ? C63 C5 H51 119.5(14) . . ? C62 O61 C69 121.69(18) . . ? O621 C62 O61 116.7(2) . . ? O621 C62 C63 125.2(2) . . ? O61 C62 C63 118.1(2) . . ? C64 C63 C62 120.2(2) . . ? C64 C63 C5 123.3(2) . . ? C62 C63 C5 116.48(19) . . ? O641 C64 C63 122.4(2) . . ? O641 C64 C70 116.9(2) . . ? C63 C64 C70 120.7(2) . . ? C64 O641 H641 109(2) . . ? C66 C65 C70 119.7(3) . . ? C66 C65 H651 123.0(17) . . ? C70 C65 H651 117.3(17) . . ? C65 C66 C67 120.5(3) . . ? C65 C66 H661 117(2) . . ? C67 C66 H661 123(2) . . ? C68 C67 C66 121.1(3) . . ? C68 C67 H671 118(2) . . ? C66 C67 H671 120(2) . . ? C67 C68 C69 118.2(3) . . ? C67 C68 H681 125.2(19) . . ? C69 C68 H681 116.6(19) . . ? O61 C69 C68 116.4(2) . . ? O61 C69 C70 121.6(2) . . ? C68 C69 C70 122.0(3) . . ? C69 C70 C65 118.4(2) . . ? C69 C70 C64 117.7(2) . . ? C65 C70 C64 123.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 N3 N4 170.05(15) . . . . ? O11 P1 N3 N4 -62.25(18) . . . . ? O21 P1 N3 N4 41.79(18) . . . . ? O2 P1 N3 C31 -12.6(2) . . . . ? O11 P1 N3 C31 115.1(2) . . . . ? O21 P1 N3 C31 -140.9(2) . . . . ? C31 N3 N4 C5 3.8(3) . . . . ? P1 N3 N4 C5 -178.77(18) . . . . ? O2 P1 O21 C22 -58.42(18) . . . . ? O11 P1 O21 C22 174.83(15) . . . . ? N3 P1 O21 C22 67.90(17) . . . . ? P1 O21 C22 C27 57.5(2) . . . . ? P1 O21 C22 C23 -126.21(19) . . . . ? C27 C22 C23 C24 0.5(3) . . . . ? O21 C22 C23 C24 -175.8(2) . . . . ? C22 C23 C24 C25 0.2(4) . . . . ? C23 C24 C25 C26 -0.8(4) . . . . ? C24 C25 C26 C27 0.7(4) . . . . ? C23 C22 C27 C26 -0.6(3) . . . . ? O21 C22 C27 C26 175.5(2) . . . . ? C25 C26 C27 C22 -0.1(4) . . . . ? O2 P1 O11 C12 -56.6(2) . . . . ? O21 P1 O11 C12 69.51(18) . . . . ? N3 P1 O11 C12 178.35(17) . . . . ? P1 O11 C12 C17 76.0(3) . . . . ? P1 O11 C12 C13 -106.7(2) . . . . ? C17 C12 C13 C14 -1.9(4) . . . . ? O11 C12 C13 C14 -179.1(2) . . . . ? C12 C13 C14 C15 0.9(5) . . . . ? C13 C14 C15 C16 0.4(5) . . . . ? C14 C15 C16 C17 -0.7(4) . . . . ? C13 C12 C17 C16 1.6(4) . . . . ? O11 C12 C17 C16 178.8(2) . . . . ? C15 C16 C17 C12 -0.2(4) . . . . ? N3 N4 C5 C63 177.08(19) . . . . ? C69 O61 C62 O621 180.0(2) . . . . ? C69 O61 C62 C63 0.4(3) . . . . ? O621 C62 C63 C64 178.5(3) . . . . ? O61 C62 C63 C64 -1.9(3) . . . . ? O621 C62 C63 C5 -4.1(4) . . . . ? O61 C62 C63 C5 175.5(2) . . . . ? N4 C5 C63 C64 0.4(3) . . . . ? N4 C5 C63 C62 -176.9(2) . . . . ? C62 C63 C64 O641 179.6(2) . . . . ? C5 C63 C64 O641 2.4(4) . . . . ? C62 C63 C64 C70 1.2(3) . . . . ? C5 C63 C64 C70 -176.0(2) . . . . ? C70 C65 C66 C67 -0.1(5) . . . . ? C65 C66 C67 C68 -0.1(5) . . . . ? C66 C67 C68 C69 0.0(5) . . . . ? C62 O61 C69 C68 -177.9(2) . . . . ? C62 O61 C69 C70 1.8(3) . . . . ? C67 C68 C69 O61 -180.0(2) . . . . ? C67 C68 C69 C70 0.3(4) . . . . ? O61 C69 C70 C65 179.8(2) . . . . ? C68 C69 C70 C65 -0.4(4) . . . . ? O61 C69 C70 C64 -2.4(3) . . . . ? C68 C69 C70 C64 177.3(2) . . . . ? C66 C65 C70 C69 0.3(4) . . . . ? C66 C65 C70 C64 -177.3(2) . . . . ? O641 C64 C70 C69 -177.6(2) . . . . ? C63 C64 C70 C69 0.9(3) . . . . ? O641 C64 C70 C65 0.0(3) . . . . ? C63 C64 C70 C65 178.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 80.08 _diffrn_measured_fraction_theta_full 0.872 _refine_diff_density_max 0.200 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.039 #==========================================================END data_comp2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C22 H17 N2 O5 P S' _chemical_formula_sum 'C22 H17 N2 O5 P S' _chemical_formula_weight 452.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.031(1) _cell_length_b 13.317(1) _cell_length_c 7.405(1) _cell_angle_alpha 100.38(1) _cell_angle_beta 95.38(1) _cell_angle_gamma 99.80(1) _cell_volume 1045.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 38.74 _cell_measurement_theta_max 39.79 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 2.430 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; de Meulenaer, Tompa (1965) ; _exptl_absorpt_correction_T_min 0.5209 _exptl_absorpt_correction_T_max 0.7913 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method 'w/ scan' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% '<2%' _diffrn_reflns_number 4197 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 72.67 _reflns_number_total 3983 _reflns_number_gt 2639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Molecular Control Software (1989a)' _computing_cell_refinement 'MSC/AFC Molecular Control Software (1989a)' _computing_data_reduction 'TEXSAN (1989b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc' _refine_ls_weighting_details ; [exp(1.20(sin\q/\l)^2^)]/[\s^2^(Fo^2^)+(0.0590P)^2^+] where P = 0.33333Fo^2^ + 0.66667Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0069(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3983 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1183 _refine_ls_wR_factor_gt 0.1120 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.80759(7) 0.87779(5) 0.04343(10) 0.0475(2) Uani 1 d . . . S2 S 0.84644(8) 0.99347(6) 0.24339(11) 0.0676(3) Uani 1 d . . . O11 O 0.67912(18) 0.79918(15) 0.0294(3) 0.0596(5) Uani 1 d . . . C12 C 0.6347(3) 0.7423(2) 0.1591(4) 0.0547(7) Uani 1 d . . . C13 C 0.5352(4) 0.6627(3) 0.0873(6) 0.0804(10) Uani 1 d . . . C14 C 0.4805(4) 0.6038(3) 0.2045(8) 0.0990(14) Uani 1 d . . . C15 C 0.5241(4) 0.6245(3) 0.3894(7) 0.0886(13) Uani 1 d . . . C16 C 0.6222(4) 0.7047(3) 0.4584(6) 0.0768(10) Uani 1 d . . . C17 C 0.6789(3) 0.7647(3) 0.3435(5) 0.0653(8) Uani 1 d . . . O21 O 0.79194(18) 0.89791(14) -0.1607(2) 0.0555(5) Uani 1 d . . . C22 C 0.7268(3) 0.97275(19) -0.2130(4) 0.0494(6) Uani 1 d . . . C23 C 0.7916(3) 1.0469(2) -0.2918(4) 0.0510(6) Uani 1 d . . . C24 C 0.7303(3) 1.1196(2) -0.3518(4) 0.0612(8) Uani 1 d . . . C25 C 0.6078(3) 1.1176(3) -0.3320(5) 0.0663(8) Uani 1 d . . . C26 C 0.5448(3) 1.0428(3) -0.2530(5) 0.0719(9) Uani 1 d . . . C27 C 0.6034(3) 0.9691(3) -0.1933(5) 0.0699(9) Uani 1 d . . . N3 N 0.9178(2) 0.80784(17) 0.0264(3) 0.0503(6) Uani 1 d . . . N4 N 0.8976(2) 0.71925(16) -0.1162(3) 0.0471(5) Uani 1 d . . . C5 C 0.9310(2) 0.7261(2) -0.2788(4) 0.0461(6) Uani 1 d . . . O61 O 0.91430(19) 0.58490(14) -0.7550(2) 0.0578(5) Uani 1 d . . . C62 C 0.9419(2) 0.6646(2) -0.6022(4) 0.0478(6) Uani 1 d . . . O621 O 0.99319(19) 0.74761(15) -0.6292(3) 0.0600(5) Uani 1 d . . . C63 C 0.9060(2) 0.64301(19) -0.4287(3) 0.0450(6) Uani 1 d . . . C64 C 0.8409(2) 0.54283(19) -0.4129(4) 0.0473(6) Uani 1 d . . . O641 O 0.8051(2) 0.52507(14) -0.2649(3) 0.0637(6) Uani 1 d . . . C65 C 0.7626(3) 0.3595(2) -0.5809(5) 0.0591(7) Uani 1 d . . . C66 C 0.7458(3) 0.2842(2) -0.7400(5) 0.0701(9) Uani 1 d . . . C67 C 0.7851(4) 0.3109(3) -0.9003(5) 0.0745(10) Uani 1 d . . . C68 C 0.8412(3) 0.4106(3) -0.9046(5) 0.0665(8) Uani 1 d . . . C69 C 0.8570(3) 0.4856(2) -0.7435(4) 0.0527(7) Uani 1 d . . . C70 C 0.8192(2) 0.46165(19) -0.5808(4) 0.0487(6) Uani 1 d . . . H51 H 0.975(2) 0.7904(19) -0.293(3) 0.048(7) Uiso 1 d . . . H31 H 0.949(3) 0.797(3) 0.115(5) 0.075(12) Uiso 1 d . . . H41 H 0.860(3) 0.655(2) -0.105(4) 0.067(9) Uiso 1 d . . . H131 H 0.506(3) 0.643(2) -0.046(5) 0.087(12) Uiso 1 d . . . H141 H 0.404(4) 0.551(3) 0.144(5) 0.101(13) Uiso 1 d . . . H151 H 0.486(4) 0.585(3) 0.474(5) 0.096(12) Uiso 1 d . . . H161 H 0.646(3) 0.711(3) 0.576(5) 0.088(13) Uiso 1 d . . . H171 H 0.742(3) 0.814(2) 0.385(4) 0.070(10) Uiso 1 d . . . H231 H 0.878(3) 1.046(2) -0.298(4) 0.074(10) Uiso 1 d . . . H241 H 0.773(3) 1.170(2) -0.412(4) 0.066(9) Uiso 1 d . . . H251 H 0.566(4) 1.165(3) -0.383(5) 0.107(13) Uiso 1 d . . . H261 H 0.465(4) 1.041(3) -0.243(5) 0.097(13) Uiso 1 d . . . H271 H 0.565(3) 0.920(2) -0.145(4) 0.064(9) Uiso 1 d . . . H651 H 0.738(3) 0.347(2) -0.465(4) 0.068(9) Uiso 1 d . . . H661 H 0.707(3) 0.211(3) -0.739(4) 0.085(11) Uiso 1 d . . . H671 H 0.769(3) 0.263(2) -1.006(4) 0.072(10) Uiso 1 d . . . H681 H 0.870(3) 0.430(2) -1.001(4) 0.067(10) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0514(4) 0.0461(4) 0.0472(4) 0.0115(3) 0.0130(3) 0.0092(3) S2 0.0835(6) 0.0534(4) 0.0628(5) 0.0003(3) 0.0198(4) 0.0107(4) O11 0.0528(11) 0.0657(12) 0.0588(12) 0.0190(9) 0.0079(9) -0.0002(9) C12 0.0481(15) 0.0470(14) 0.074(2) 0.0181(13) 0.0194(14) 0.0102(12) C13 0.082(2) 0.065(2) 0.088(3) 0.0076(19) 0.020(2) -0.0019(18) C14 0.088(3) 0.067(2) 0.137(4) 0.021(2) 0.035(3) -0.013(2) C15 0.085(3) 0.078(2) 0.125(4) 0.057(3) 0.047(3) 0.022(2) C16 0.065(2) 0.099(3) 0.088(3) 0.053(2) 0.026(2) 0.030(2) C17 0.0484(17) 0.079(2) 0.073(2) 0.0328(17) 0.0092(16) 0.0041(16) O21 0.0674(13) 0.0619(11) 0.0485(11) 0.0218(9) 0.0165(9) 0.0277(10) C22 0.0564(16) 0.0477(14) 0.0472(15) 0.0100(11) 0.0079(12) 0.0173(12) C23 0.0519(16) 0.0500(14) 0.0516(16) 0.0102(12) 0.0078(13) 0.0106(12) C24 0.072(2) 0.0504(16) 0.0627(19) 0.0152(13) 0.0112(16) 0.0114(15) C25 0.075(2) 0.0636(19) 0.065(2) 0.0126(15) 0.0055(17) 0.0291(17) C26 0.054(2) 0.090(2) 0.080(2) 0.0230(19) 0.0144(17) 0.0301(18) C27 0.0590(19) 0.075(2) 0.087(2) 0.0333(19) 0.0245(17) 0.0173(17) N3 0.0556(14) 0.0502(12) 0.0463(14) 0.0109(10) 0.0058(11) 0.0125(11) N4 0.0594(14) 0.0382(11) 0.0465(12) 0.0097(9) 0.0151(10) 0.0111(10) C5 0.0444(14) 0.0482(14) 0.0507(15) 0.0190(11) 0.0095(11) 0.0109(11) O61 0.0748(13) 0.0551(10) 0.0468(11) 0.0154(8) 0.0170(9) 0.0110(10) C62 0.0481(15) 0.0530(15) 0.0474(15) 0.0174(12) 0.0097(12) 0.0140(12) O621 0.0680(13) 0.0595(11) 0.0560(12) 0.0243(9) 0.0141(10) 0.0049(10) C63 0.0444(14) 0.0491(14) 0.0470(14) 0.0161(11) 0.0107(11) 0.0143(11) C64 0.0508(15) 0.0464(13) 0.0504(15) 0.0156(11) 0.0150(12) 0.0135(11) O641 0.0840(15) 0.0533(11) 0.0547(12) 0.0161(9) 0.0247(10) 0.0017(10) C65 0.0617(18) 0.0510(15) 0.067(2) 0.0165(14) 0.0127(15) 0.0116(13) C66 0.077(2) 0.0498(17) 0.077(2) 0.0056(15) 0.0006(18) 0.0070(16) C67 0.093(3) 0.063(2) 0.058(2) -0.0055(16) -0.0017(18) 0.0162(18) C68 0.085(2) 0.0678(19) 0.0496(18) 0.0106(14) 0.0101(17) 0.0215(17) C69 0.0580(17) 0.0535(15) 0.0516(16) 0.0153(12) 0.0093(13) 0.0177(13) C70 0.0503(15) 0.0468(14) 0.0512(16) 0.0107(11) 0.0089(12) 0.0131(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O21 1.5811(18) . ? P1 O11 1.595(2) . ? P1 N3 1.654(2) . ? P1 S2 1.8931(10) . ? O11 C12 1.400(3) . ? C12 C17 1.367(4) . ? C12 C13 1.379(4) . ? C13 C14 1.384(5) . ? C13 H131 0.98(3) . ? C14 C15 1.370(6) . ? C14 H141 1.01(4) . ? C15 C16 1.371(6) . ? C15 H151 0.97(4) . ? C16 C17 1.389(4) . ? C16 H161 0.87(3) . ? C17 H171 0.86(3) . ? O21 C22 1.411(3) . ? C22 C23 1.368(4) . ? C22 C27 1.377(4) . ? C23 C24 1.383(4) . ? C23 H231 0.96(3) . ? C24 C25 1.370(5) . ? C24 H241 0.96(3) . ? C25 C26 1.367(5) . ? C25 H251 0.95(4) . ? C26 C27 1.377(5) . ? C26 H261 0.89(4) . ? C27 H271 0.87(3) . ? N3 N4 1.405(3) . ? N3 H31 0.76(3) . ? N4 C5 1.306(3) . ? N4 H41 0.91(3) . ? C5 C63 1.389(3) . ? C5 H51 0.94(3) . ? O61 C62 1.375(3) . ? O61 C69 1.386(3) . ? C62 O621 1.213(3) . ? C62 C63 1.442(3) . ? C63 C64 1.433(3) . ? C64 O641 1.247(3) . ? C64 C70 1.464(3) . ? C65 C66 1.378(4) . ? C65 C70 1.396(4) . ? C65 H651 0.96(3) . ? C66 C67 1.385(5) . ? C66 H661 1.00(3) . ? C67 C68 1.372(5) . ? C67 H671 0.90(3) . ? C68 C69 1.387(4) . ? C68 H681 0.87(3) . ? C69 C70 1.384(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O21 P1 O11 97.46(11) . . ? O21 P1 N3 99.46(11) . . ? O11 P1 N3 107.42(11) . . ? O21 P1 S2 118.78(8) . . ? O11 P1 S2 117.99(8) . . ? N3 P1 S2 113.16(10) . . ? C12 O11 P1 129.07(19) . . ? C17 C12 C13 121.3(3) . . ? C17 C12 O11 124.6(3) . . ? C13 C12 O11 114.0(3) . . ? C12 C13 C14 119.1(4) . . ? C12 C13 H131 122(2) . . ? C14 C13 H131 119(2) . . ? C15 C14 C13 120.5(4) . . ? C15 C14 H141 125(2) . . ? C13 C14 H141 114(2) . . ? C14 C15 C16 119.5(4) . . ? C14 C15 H151 122(2) . . ? C16 C15 H151 119(2) . . ? C15 C16 C17 121.0(4) . . ? C15 C16 H161 114(2) . . ? C17 C16 H161 125(3) . . ? C12 C17 C16 118.6(3) . . ? C12 C17 H171 120(2) . . ? C16 C17 H171 122(2) . . ? C22 O21 P1 123.18(16) . . ? C23 C22 C27 121.6(3) . . ? C23 C22 O21 116.3(2) . . ? C27 C22 O21 122.0(3) . . ? C22 C23 C24 118.4(3) . . ? C22 C23 H231 117.0(19) . . ? C24 C23 H231 124.6(19) . . ? C25 C24 C23 120.8(3) . . ? C25 C24 H241 119.6(18) . . ? C23 C24 H241 119.5(18) . . ? C26 C25 C24 119.8(3) . . ? C26 C25 H251 121(2) . . ? C24 C25 H251 119(2) . . ? C25 C26 C27 120.6(3) . . ? C25 C26 H261 119(2) . . ? C27 C26 H261 120(2) . . ? C26 C27 C22 118.8(3) . . ? C26 C27 H271 122(2) . . ? C22 C27 H271 119(2) . . ? N4 N3 P1 117.8(2) . . ? N4 N3 H31 110(3) . . ? P1 N3 H31 118(3) . . ? C5 N4 N3 120.5(2) . . ? C5 N4 H41 115.4(19) . . ? N3 N4 H41 124.1(19) . . ? N4 C5 C63 123.2(2) . . ? N4 C5 H51 117.6(15) . . ? C63 C5 H51 119.3(15) . . ? C62 O61 C69 121.6(2) . . ? O621 C62 O61 115.5(2) . . ? O621 C62 C63 126.4(2) . . ? O61 C62 C63 118.1(2) . . ? C5 C63 C64 121.2(2) . . ? C5 C63 C62 116.6(2) . . ? C64 C63 C62 122.1(2) . . ? O641 C64 C63 122.3(2) . . ? O641 C64 C70 121.5(2) . . ? C63 C64 C70 116.2(2) . . ? C66 C65 C70 120.4(3) . . ? C66 C65 H651 124.2(17) . . ? C70 C65 H651 115.4(17) . . ? C65 C66 C67 119.3(3) . . ? C65 C66 H661 120.3(19) . . ? C67 C66 H661 120.4(19) . . ? C68 C67 C66 121.7(3) . . ? C68 C67 H671 119(2) . . ? C66 C67 H671 119(2) . . ? C67 C68 C69 118.3(3) . . ? C67 C68 H681 125(2) . . ? C69 C68 H681 117(2) . . ? C70 C69 O61 122.3(2) . . ? C70 C69 C68 121.6(3) . . ? O61 C69 C68 116.1(3) . . ? C69 C70 C65 118.7(3) . . ? C69 C70 C64 119.6(2) . . ? C65 C70 C64 121.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O21 P1 O11 C12 174.3(2) . . . . ? N3 P1 O11 C12 71.9(2) . . . . ? S2 P1 O11 C12 -57.4(2) . . . . ? P1 O11 C12 C17 18.8(4) . . . . ? P1 O11 C12 C13 -164.5(2) . . . . ? C17 C12 C13 C14 -0.8(5) . . . . ? O11 C12 C13 C14 -177.5(3) . . . . ? C12 C13 C14 C15 0.3(6) . . . . ? C13 C14 C15 C16 0.4(7) . . . . ? C14 C15 C16 C17 -0.6(6) . . . . ? C13 C12 C17 C16 0.5(5) . . . . ? O11 C12 C17 C16 176.9(3) . . . . ? C15 C16 C17 C12 0.2(5) . . . . ? O11 P1 O21 C22 84.6(2) . . . . ? N3 P1 O21 C22 -166.2(2) . . . . ? S2 P1 O21 C22 -43.1(2) . . . . ? P1 O21 C22 C23 123.0(2) . . . . ? P1 O21 C22 C27 -59.7(4) . . . . ? C27 C22 C23 C24 0.2(4) . . . . ? O21 C22 C23 C24 177.6(2) . . . . ? C22 C23 C24 C25 0.3(5) . . . . ? C23 C24 C25 C26 -0.3(5) . . . . ? C24 C25 C26 C27 -0.1(6) . . . . ? C25 C26 C27 C22 0.6(6) . . . . ? C23 C22 C27 C26 -0.6(5) . . . . ? O21 C22 C27 C26 -177.9(3) . . . . ? O21 P1 N3 N4 -53.8(2) . . . . ? O11 P1 N3 N4 47.2(2) . . . . ? S2 P1 N3 N4 179.18(16) . . . . ? P1 N3 N4 C5 89.5(3) . . . . ? N3 N4 C5 C63 -175.5(2) . . . . ? C69 O61 C62 O621 179.2(2) . . . . ? C69 O61 C62 C63 -1.9(4) . . . . ? N4 C5 C63 C64 -0.2(4) . . . . ? N4 C5 C63 C62 176.1(2) . . . . ? O621 C62 C63 C5 1.1(4) . . . . ? O61 C62 C63 C5 -177.7(2) . . . . ? O621 C62 C63 C64 177.4(3) . . . . ? O61 C62 C63 C64 -1.4(4) . . . . ? C5 C63 C64 O641 -0.8(4) . . . . ? C62 C63 C64 O641 -176.9(3) . . . . ? C5 C63 C64 C70 179.5(2) . . . . ? C62 C63 C64 C70 3.4(4) . . . . ? C70 C65 C66 C67 -0.3(5) . . . . ? C65 C66 C67 C68 0.4(6) . . . . ? C66 C67 C68 C69 -0.7(6) . . . . ? C62 O61 C69 C70 3.0(4) . . . . ? C62 O61 C69 C68 -176.1(3) . . . . ? C67 C68 C69 C70 0.8(5) . . . . ? C67 C68 C69 O61 179.9(3) . . . . ? O61 C69 C70 C65 -179.7(3) . . . . ? C68 C69 C70 C65 -0.7(4) . . . . ? O61 C69 C70 C64 -0.7(4) . . . . ? C68 C69 C70 C64 178.3(3) . . . . ? C66 C65 C70 C69 0.5(4) . . . . ? C66 C65 C70 C64 -178.5(3) . . . . ? O641 C64 C70 C69 178.0(3) . . . . ? C63 C64 C70 C69 -2.4(4) . . . . ? O641 C64 C70 C65 -3.0(4) . . . . ? C63 C64 C70 C65 176.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 72.67 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.205 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.043